America's Happiest Seaside Towns

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Protected Paradise

Old Saybrook, Connecticut

A classic American Main Street and water everywhere, it's the kind of town you thought didn't exist anymore. A well-placed sandbar kept this area from developing into a major seaport. What developed instead was a tidy coastal New England town, where Main Street still has real stores, not just boutiques, and stately old hardwoods canopy the quieter avenues that meander down toward the sound.